WO2004019910A2 - Buccal, polar and non-polar spray or capsule containing drugs for treating disorders of the gastrointestinal tract or urinary tract - Google Patents
Buccal, polar and non-polar spray or capsule containing drugs for treating disorders of the gastrointestinal tract or urinary tractInfo
- Publication number
- WO2004019910A2 WO2004019910A2 PCT/US2003/026854 US0326854W WO2004019910A2 WO 2004019910 A2 WO2004019910 A2 WO 2004019910A2 US 0326854 W US0326854 W US 0326854W WO 2004019910 A2 WO2004019910 A2 WO 2004019910A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- active compound
- group
- mixtures
- amount
- Prior art date
Links
- 239000007921 spray Substances 0.000 title claims abstract description 61
- 229940079593 drug Drugs 0.000 title claims description 14
- 239000003814 drug Substances 0.000 title claims description 14
- 239000002775 capsule Substances 0.000 title abstract description 27
- 210000001035 gastrointestinal tract Anatomy 0.000 title description 2
- 210000001635 urinary tract Anatomy 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 227
- 150000001875 compounds Chemical class 0.000 claims abstract description 134
- 239000000796 flavoring agent Substances 0.000 claims abstract description 79
- 239000003380 propellant Substances 0.000 claims abstract description 44
- 235000013355 food flavoring agent Nutrition 0.000 claims abstract description 35
- 239000002798 polar solvent Substances 0.000 claims abstract description 30
- 239000012454 non-polar solvent Substances 0.000 claims abstract description 22
- 210000002200 mouth mucosa Anatomy 0.000 claims abstract description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 76
- 239000003795 chemical substances by application Substances 0.000 claims description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
- -1 propatheline Chemical compound 0.000 claims description 33
- 229920001223 polyethylene glycol Polymers 0.000 claims description 28
- 230000002686 anti-diuretic effect Effects 0.000 claims description 26
- 229940124538 antidiuretic agent Drugs 0.000 claims description 26
- 239000002202 Polyethylene glycol Substances 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 18
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims description 13
- 102000004190 Enzymes Human genes 0.000 claims description 13
- 108090000790 Enzymes Proteins 0.000 claims description 13
- 206010028813 Nausea Diseases 0.000 claims description 13
- 206010046543 Urinary incontinence Diseases 0.000 claims description 13
- 206010047700 Vomiting Diseases 0.000 claims description 13
- 230000002921 anti-spasmodic effect Effects 0.000 claims description 13
- 239000003613 bile acid Substances 0.000 claims description 13
- 229940088598 enzyme Drugs 0.000 claims description 13
- 208000001130 gallstones Diseases 0.000 claims description 13
- 230000008693 nausea Effects 0.000 claims description 13
- 210000002460 smooth muscle Anatomy 0.000 claims description 13
- 239000002731 stomach secretion inhibitor Substances 0.000 claims description 13
- 230000008673 vomiting Effects 0.000 claims description 13
- 239000003160 antidiuretic agent Substances 0.000 claims description 12
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 12
- FELGMEQIXOGIFQ-CYBMUJFWSA-N (3r)-9-methyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1h-carbazol-4-one Chemical compound CC1=NC=CN1C[C@@H]1C(=O)C(C=2C(=CC=CC=2)N2C)=C2CC1 FELGMEQIXOGIFQ-CYBMUJFWSA-N 0.000 claims description 11
- 229930195733 hydrocarbon Natural products 0.000 claims description 11
- 150000002430 hydrocarbons Chemical class 0.000 claims description 11
- 229960005343 ondansetron Drugs 0.000 claims description 11
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 claims description 10
- 229930003347 Atropine Natural products 0.000 claims description 10
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 claims description 10
- XIQVNETUBQGFHX-UHFFFAOYSA-N Ditropan Chemical compound C=1C=CC=CC=1C(O)(C(=O)OCC#CCN(CC)CC)C1CCCCC1 XIQVNETUBQGFHX-UHFFFAOYSA-N 0.000 claims description 10
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 claims description 10
- STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 0.000 claims description 10
- 102100033342 Lysosomal acid glucosylceramidase Human genes 0.000 claims description 10
- STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 claims description 10
- IQPSEEYGBUAQFF-UHFFFAOYSA-N Pantoprazole Chemical compound COC1=CC=NC(CS(=O)C=2NC3=CC=C(OC(F)F)C=C3N=2)=C1OC IQPSEEYGBUAQFF-UHFFFAOYSA-N 0.000 claims description 10
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 claims description 10
- 229960000396 atropine Drugs 0.000 claims description 10
- 229960001596 famotidine Drugs 0.000 claims description 10
- XUFQPHANEAPEMJ-UHFFFAOYSA-N famotidine Chemical compound NC(N)=NC1=NC(CSCCC(N)=NS(N)(=O)=O)=CS1 XUFQPHANEAPEMJ-UHFFFAOYSA-N 0.000 claims description 10
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 10
- 229960003174 lansoprazole Drugs 0.000 claims description 10
- MJIHNNLFOKEZEW-UHFFFAOYSA-N lansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1 MJIHNNLFOKEZEW-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- OJLOPKGSLYJEMD-URPKTTJQSA-N methyl 7-[(1r,2r,3r)-3-hydroxy-2-[(1e)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl]heptanoate Chemical compound CCCCC(C)(O)C\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC OJLOPKGSLYJEMD-URPKTTJQSA-N 0.000 claims description 10
- 229960005249 misoprostol Drugs 0.000 claims description 10
- 239000003921 oil Substances 0.000 claims description 10
- 235000019198 oils Nutrition 0.000 claims description 10
- 229960000381 omeprazole Drugs 0.000 claims description 10
- 229960005434 oxybutynin Drugs 0.000 claims description 10
- 229960005019 pantoprazole Drugs 0.000 claims description 10
- STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 claims description 10
- 229960002646 scopolamine Drugs 0.000 claims description 10
- 229960003688 tropisetron Drugs 0.000 claims description 10
- 241000124008 Mammalia Species 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- PWWVAXIEGOYWEE-UHFFFAOYSA-N Isophenergan Chemical compound C1=CC=C2N(CC(C)N(C)C)C3=CC=CC=C3SC2=C1 PWWVAXIEGOYWEE-UHFFFAOYSA-N 0.000 claims description 7
- OCJYIGYOJCODJL-UHFFFAOYSA-N Meclizine Chemical compound CC1=CC=CC(CN2CCN(CC2)C(C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)=C1 OCJYIGYOJCODJL-UHFFFAOYSA-N 0.000 claims description 7
- 229940124575 antispasmodic agent Drugs 0.000 claims description 7
- 229960001380 cimetidine Drugs 0.000 claims description 7
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 claims description 7
- 229960001474 meclozine Drugs 0.000 claims description 7
- 229960003910 promethazine Drugs 0.000 claims description 7
- BVPWJMCABCPUQY-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxy-N-[1-(phenylmethyl)-4-piperidinyl]benzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NC1CCN(CC=2C=CC=CC=2)CC1 BVPWJMCABCPUQY-UHFFFAOYSA-N 0.000 claims description 6
- KPYSYYIEGFHWSV-UHFFFAOYSA-N Baclofen Chemical compound OC(=O)CC(CN)C1=CC=C(Cl)C=C1 KPYSYYIEGFHWSV-UHFFFAOYSA-N 0.000 claims description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 229960000794 baclofen Drugs 0.000 claims description 6
- 239000001273 butane Substances 0.000 claims description 6
- 239000000812 cholinergic antagonist Substances 0.000 claims description 6
- 230000003381 solubilizing effect Effects 0.000 claims description 6
- XFYDIVBRZNQMJC-UHFFFAOYSA-N tizanidine Chemical compound ClC=1C=CC2=NSN=C2C=1NC1=NCCN1 XFYDIVBRZNQMJC-UHFFFAOYSA-N 0.000 claims description 6
- 229960000488 tizanidine Drugs 0.000 claims description 6
- TWHNMSJGYKMTRB-KXYUELECSA-N (2r,3r)-2,3-dihydroxybutanedioic acid;2-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-methylphenol Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C)C=2)O)=CC=CC=C1 TWHNMSJGYKMTRB-KXYUELECSA-N 0.000 claims description 5
- BWNLUIXQIHPUGO-RDTXWAMCSA-N (2r,4r)-4-(dimethylamino)-2-phenyl-2-pyridin-2-ylpentanamide Chemical compound C1([C@](C(N)=O)(C[C@@H](C)N(C)C)C=2N=CC=CC=2)=CC=CC=C1 BWNLUIXQIHPUGO-RDTXWAMCSA-N 0.000 claims description 5
- RUDATBOHQWOJDD-UHFFFAOYSA-N (3beta,5beta,7alpha)-3,7-Dihydroxycholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 RUDATBOHQWOJDD-UHFFFAOYSA-N 0.000 claims description 5
- DJAHKBBSJCDSOZ-AJLBTXRUSA-N (5z,9e,13e)-6,10,14,18-tetramethylnonadeca-5,9,13,17-tetraen-2-one;(5e,9e,13e)-6,10,14,18-tetramethylnonadeca-5,9,13,17-tetraen-2-one Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C/CCC(C)=O.CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CCC(C)=O DJAHKBBSJCDSOZ-AJLBTXRUSA-N 0.000 claims description 5
- JIVPVXMEBJLZRO-CQSZACIVSA-N 2-chloro-5-[(1r)-1-hydroxy-3-oxo-2h-isoindol-1-yl]benzenesulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC([C@@]2(O)C3=CC=CC=C3C(=O)N2)=C1 JIVPVXMEBJLZRO-CQSZACIVSA-N 0.000 claims description 5
- 239000004382 Amylase Substances 0.000 claims description 5
- 102000013142 Amylases Human genes 0.000 claims description 5
- 108010065511 Amylases Proteins 0.000 claims description 5
- 235000019499 Citrus oil Nutrition 0.000 claims description 5
- 108010000437 Deamino Arginine Vasopressin Proteins 0.000 claims description 5
- 102000004627 Iduronidase Human genes 0.000 claims description 5
- 108010003381 Iduronidase Proteins 0.000 claims description 5
- 102000004882 Lipase Human genes 0.000 claims description 5
- 239000004367 Lipase Substances 0.000 claims description 5
- 108090001060 Lipase Proteins 0.000 claims description 5
- 235000014749 Mentha crispa Nutrition 0.000 claims description 5
- 244000246386 Mentha pulegium Species 0.000 claims description 5
- 235000016257 Mentha pulegium Nutrition 0.000 claims description 5
- 244000078639 Mentha spicata Species 0.000 claims description 5
- 235000004357 Mentha x piperita Nutrition 0.000 claims description 5
- CESYKOGBSMNBPD-UHFFFAOYSA-N Methyclothiazide Chemical compound ClC1=C(S(N)(=O)=O)C=C2S(=O)(=O)N(C)C(CCl)NC2=C1 CESYKOGBSMNBPD-UHFFFAOYSA-N 0.000 claims description 5
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- 101800000989 Oxytocin Proteins 0.000 claims description 5
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- CYLWJCABXYDINA-UHFFFAOYSA-N Polythiazide Polymers ClC1=C(S(N)(=O)=O)C=C2S(=O)(=O)N(C)C(CSCC(F)(F)F)NC2=C1 CYLWJCABXYDINA-UHFFFAOYSA-N 0.000 claims description 5
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- NGBFQHCMQULJNZ-UHFFFAOYSA-N Torsemide Chemical compound CC(C)NC(=O)NS(=O)(=O)C1=CN=CC=C1NC1=CC=CC(C)=C1 NGBFQHCMQULJNZ-UHFFFAOYSA-N 0.000 claims description 5
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- FLZQKRKHLSUHOR-UHFFFAOYSA-N alosetron Chemical compound CC1=NC=N[C]1CN1C(=O)C(C=2C(=CC=CC=2)N2C)=C2CC1 FLZQKRKHLSUHOR-UHFFFAOYSA-N 0.000 claims description 5
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- 235000019418 amylase Nutrition 0.000 claims description 5
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- HDWIHXWEUNVBIY-UHFFFAOYSA-N bendroflumethiazidum Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)N)=CC(S(N2)(=O)=O)=C1NC2CC1=CC=CC=C1 HDWIHXWEUNVBIY-UHFFFAOYSA-N 0.000 claims description 5
- NDTSRXAMMQDVSW-UHFFFAOYSA-N benzthiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(S(N2)(=O)=O)=C1N=C2CSCC1=CC=CC=C1 NDTSRXAMMQDVSW-UHFFFAOYSA-N 0.000 claims description 5
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- 229910052797 bismuth Inorganic materials 0.000 claims description 5
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- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 239000003485 histamine H2 receptor antagonist Substances 0.000 description 1
- 229940077716 histamine h2 receptor antagonists for peptic ulcer and gord Drugs 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 229940039009 isoproterenol Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229960000509 metaxalone Drugs 0.000 description 1
- 229960002330 methocarbamol Drugs 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 229940045641 monobasic sodium phosphate Drugs 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- ACTNHJDHMQSOGL-UHFFFAOYSA-N n',n'-dibenzylethane-1,2-diamine Chemical compound C=1C=CC=CC=1CN(CCN)CC1=CC=CC=C1 ACTNHJDHMQSOGL-UHFFFAOYSA-N 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229960003941 orphenadrine Drugs 0.000 description 1
- QVYRGXJJSLMXQH-UHFFFAOYSA-N orphenadrine Chemical compound C=1C=CC=C(C)C=1C(OCCN(C)C)C1=CC=CC=C1 QVYRGXJJSLMXQH-UHFFFAOYSA-N 0.000 description 1
- 239000000813 peptide hormone Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000003772 serotonin uptake inhibitor Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 229960000999 sodium citrate dihydrate Drugs 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical compound OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 229940066767 systemic antihistamines phenothiazine derivative Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
- 239000003451 thiazide diuretic agent Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 235000016788 valerian Nutrition 0.000 description 1
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- 229940124549 vasodilator Drugs 0.000 description 1
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- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
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- 239000011701 zinc Substances 0.000 description 1
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Classifications
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Definitions
- a chewable gelatin capsule containing a solution or dispersion of a drug is described in U.S.P. 4,935,243, Borkan et al. U.S.P. 4,919,919, Aouda et al, and U.S.P. 5,370,862, Klokkers-Bethke, describe a nitroglycerin spray for administration to the oral mucosa comprising nitroglycerin, ethanol, and other components.
- An orally administered pump spray is described by Cholcha in U.S.P. 5, 186,925.
- Aerosol compositions containing a hydrocarbon propellant and a drug for administration to a mucosal surface are described in U.K. 2,082,457, Su, U.S.P.
- buccal aerosol spray or soft bite gelatin capsule using a polar or non-polar solvent has now been developed which provides biologically active compounds for rapid absorption through the oral mucosa, resulting in fast onset of effect.
- the buccal aerosol spray compositions of the present invention for transmucosal administration of a pharmacologically active compound soluble in a pharmacologically acceptable non-polar solvent comprise in weight % of total composition: pharmaceutically acceptable propellant 5-80 %, nonpolar solvent 19-85 %, active compound 0.05-50 %, suitably additionally comprising, by weight of total composition a flavoring agent 0.01-10 %.
- the composition comprises: propellant 10-70 %, non-polar solvent 25-89.9 %, active compound 0.01-40 %, flavoring agent 1-8 %; most suitably propellant 20-70 %, non-polar solvent 25-74.75 %, active compound 0.25-35 %, flavoring agent 2-7.5 %.
- the buccal polar aerosol spray compositions of the present invention, for transmucosal administration of a pharmacologically active compound soluble in a pharmacologically acceptable polar solvent are also administrable in aerosol form driven by a propellant.
- the composition comprises in weight % of total composition: aqueous polar solvent 10-97 %, active compound 0.1-25 %, suitably additionally comprising, by weight of total composition a flavoring agent 0.05-10 % and propellant: 2 - 10 %.
- the composition comprises: polar solvent 20-97 %, active compound 0.1- 15%, flavoring agent 0.1-5 % and propellant 2-5 %; most suitably polar solvent 25-97 %, active compound 0.2-25 %, flavoring agent 0.1-2.5 % and propellant 2-4 %.
- the buccal pump spray composition of the present invention i.e., the propellant free composition, for transmucosal administration of a pharmacologically active compound wherein said active compound is soluble in a pharmacologically acceptable non- polar solvent comprises in weight % of total composition: non-polar solvent 30-99.69 %, active compound 0.005-55 %, and suitably additionally, flavoring agent 0.1-10 %.
- the composition comprises: polar solvent 37-98.58 %, active compound 0.005-55 %, flavoring agent 0.5-8 %; most suitably polar solvent 60.9-97.06 %, active compound 0.01-40 %, flavoring agent 0.75-7.5 %.
- the soft bite gelatin capsules of the present invention for transmucosal administration of a pharmacologically active compound, at least partially soluble in a pharmacologically acceptable non-polar solvent, having charged thereto a fill composition comprise in weight % of total composition: non-polar solvent 4-99.99 %, emulsifier 0-20 %, active compound 0.01-80 %, provided that said fill composition contains less than 10 % of water, suitably additionally comprising, by weight of the composition: flavoring agent 0.01- 10 %.
- the soft bite gelatin capsule comprises: non-polar solvent 21.5-99.975 %, emulsifier 0-15 %, active compound 0.025-70 %, flavoring agent 1-8 %; most suitably: nonpolar solvent 28.5-97.9 %, emulsifier 0-10 %, active compound 0.1-65.0 %, flavoring agent 2-6 %.
- the soft bite gelatin capsule comprises: polar solvent 37-99.95 %, emulsifier 0-15 %, active compound 0.025-55 %, flavoring agent 1-8 %; most suitably: polar solvent 44-96.925 %, emulsifier 0-10 %, active compound 0.075-50 %, flavoring agent 2-6 %.
- a further object is a sealed aerosol spray container containing a composition of the non polar or polar aerosol spray formulation, and a metered valve suitable for releasing from said container a predetermined amount of said composition.
- the propellant is a non-Freon material, preferably a C 3 . 8 hydrocarbon of a linear or branched configuration.
- the propellant should be substantially non-aqueous.
- the propellant produces a pressure in the aerosol container such that under expected nomial usage it will produce sufficient pressure to expel the solvent from the container when the valve is activated but not excessive pressure such as to damage the container or valve seals.
- the non-polar solvent is a non-polar hydrocarbon, preferably a C 7 . 18 hydrocarbon of a linear or branched configuration, fatty acid esters, and triglycerides, such as miglyol.
- the solvent must dissolve the active compound and be miscible with the propellant, i. e. , solvent and propellant must form a single phase at a temperature of 0-40°C a pressure range of between 1-3 atm.
- the polar and non-polar aerosol spray compositions of the invention are intended to be administered from a sealed, pressurized container. Unlike a pump spray, which allows the entry of air into the container after every activation, the aerosol container of the invention is sealed at the time of manufacture. The contents of the container are released by activation of a metered valve, which does not allow entry of atmospheric gasses with each activation.
- a metered valve which does not allow entry of atmospheric gasses with each activation.
- a further object is a pump spray container containing a composition of the pump spray formulation, and a metered valve suitable for releasing from said container a predetermined amount of said composition.
- a further object is a soft gelatin bite capsule containing a composition of as set forth above.
- the formulation may be in the form of a viscous solution or paste containing the active compounds. Although solutions are prefened, paste fills may also be used where the active compound is not soluble or only partially soluble in the solvent of choice. Where water is used to form part of the paste composition, it should not exceed 10 % thereof. (All percentages herein are by weight unless otherwise indicated.)
- the polar or non-polar solvent is chosen such that it is compatible with the gelatin shell and the active compound.
- the solvent preferably dissolves the active compound.
- other components wherein the active compound is not soluble or only slightly soluble may be used and will form a paste fill.
- Soft gelatin capsules are well known in the art. See, for example, U.S.P.
- the capsules of the present invention are intended to be bitten into to release the low viscosity solution or paste therein, which will then coat the buccal mucosa with the active compounds.
- Typical capsules which are swallowed whole or bitten and then swallowed, deliver the active compounds to the stomach, which results in significant lag time before maximum blood levels can be achieved or subject the compound to a large first pass effect. Because of the enhanced absorption of the compounds through the oral mucosa and no chance of a first pass effect, use of the bite capsules of the invention will eliminate much of the lag time, resulting in hastened onset of biological effect.
- the shell of a soft gelatin capsule of the invention may comprise, for example: gelatin: 50-75 %, glycerin 20-30 %, colorants 0.5-1.5 %, water 5-10 %, and sorbitol 2-10 %.
- the active compound may include, biologically active peptides, central nervous system active amines, sulfonyl ureas, antibiotics, antifungals, antivirals, sleep inducers, antiasthmatics, bronchial dilators, antiemetics, histamine H-2 receptor antagonists, barbiturates, prostaglandins and neutraceuticals.
- the active compounds may also include antihistamines, alkaloids, hormones, benzodiazepines and narcotic analgesics. While not limited thereto, these active compounds are particularly suitable for non-polar pump spray formulation and application.
- the active compounds may also include anti-diuretics, anti-muscle spasm agents, anti-spasmodics, agents for treating urinary incontinence, anti-diarrheal agents, agents for treating nausea and/or vomiting, smooth muscle contractile agents, anti-secretory agents, enzymes, anti-diuretics, anti-ulcerants, bile acid replacement and/or gallstone solubilizing drugs, or mixtures thereof.
- FIG 1. is a schematic diagram showing routes of absorption and processing of pharmacologically active substances in a mammalian system.
- the preferred active compounds of the present invention are in an ionized, salt form or as the free base of the pharmaceutically acceptable salts thereof (provided, for the aerosol or pump spray compositions, they are soluble in the spray solvent). These compounds are soluble in the non-polar solvents of the invention at useful concentrations or can be prepared as pastes at useful concentrations. These concentrations may be less than the standard accepted dose for these compounds since there is enhanced absorption of the compounds through the oral mucosa. This aspect of the invention is especially important when there is a large (40-99.99%) first pass effect.
- propellants for the non polar sprays propane, N-butane, iso-butane, N- pentane, iso-pentane, and neo-pentane, and mixtures thereof may be used.
- N-butane and iso-butane, as single gases, are the preferred propellants. It is permissible for the propellant to have a water content of no more than 0.2%, typically 0.1-0.2%. All percentages herein are by weight unless otherwise indicated. It is also preferable that the propellant be synthetically produced to minimize the presence of contaminants which are harmful to the active compounds. These contaminants include oxidizing agents, reducing agents, Lewis acids or bases, and water. The concentration of each of these should be less than 0.1 %, except that water may be as high as 0.2%.
- Suitable non-polar solvents for the capsules and the non-polar sprays include (C 2 -C 24 ) fatty acid (C 2 -C 6 ) esters, C 7 -C 18 hydrocarbon, C 2 -C 6 alkanoyl esters, and the triglycerides of the corresponding acids.
- other liquid components may be used instead of the above low molecular weight solvents. These include soya oil, corn oil, other vegetable oils.
- solvents for the polar capsules or sprays there may be used low molecular weight polyethyleneglycols (PEG) of 400-1000 Mw (preferably 400-600), low molecular weight (C 2 -C 8 ) mono and polyols and alcohols of C 7 -C 18 linear or branch chain hydrocarbons, glycerin may also be present and water may also be used in the sprays, but only in limited amount in the capsules.
- PEG polyethyleneglycols
- C 2 -C 8 low molecular weight mono and polyols and alcohols of C 7 -C 18 linear or branch chain hydrocarbons
- glycerin may also be present and water may also be used in the sprays, but only in limited amount in the capsules.
- the preferred flavoring agents are synthetic or natural oil of peppermint, oil of spearmint, citrus oil, fruit flavors, sweeteners (sugars, aspartame, saccharin, etc.), and combinations thereof.
- the active substances include the active compounds selected from the group consisting of cyclosporine, sermorelin, octreotide acetate, calcitonin-salmon, insulin lispro, sumatriptan succinate, clozepine, cyclobenzaprine, dexfenfluramine hydrochloride, glyburide, zidovudine, erythromycin, ciprofloxacin, ondansetron hydrochloride, dimenhydrinate, cimetidine hydrochloride, famotidine, phenytoin sodium, phenytoin, carboprost thromethamine, carboprost, diphenhydramine hydrochloride, isoproterenol hydrochloride, terbutaline s
- the active compound is an anti-diuretic, anti-muscle spasm agent, anti-spasmodic, agent for treating urinary incontinence, anti-diarrheal agent, agent for treating nausea and/or vomiting, smooth muscle contractile agent, anti-secretory agent, enzyme, anti-diuretic, anti-ulcerant, bile acid replacement and/or gallstone solubilizing drug, or a mixture thereof
- the active compound is an anti-diuretic.
- Suitable anti- diuretics for use in the buccal sprays of the invention include, but are not limited to, acetazolamide, benzthiazide, bendroflumethazide, bumetanide, chlorthalidone, chlorothiazide, ethacrynic acid, furosemide, hydrochlorothiazide, hydroflumethiazide, methyclothiazide, polythiazide, quinethazone, spironolactone, triamterene, torsemide, trichlomethiazide, and mixtures thereof.
- the active compound is an anti-muscle spasm agent.
- Suitable anti-muscle spasm agents for use in the buccal sprays of the invention include, but are not limited to, baclofen, botulinum toxin, carisoprodol, chlorphenesin, chlorzoxazone, cyclobenzaprine, dantrolene, diazepam, metaxalone, methocarbamol, orphenadrine, tizanidine, and mixtures thereof.
- the active compound is an anti-spasmodic.
- Suitable anti- spasmodics for use in the buccal sprays of the invention include, but are not limited to, atropine, baclofen, dicyclomine, hyoscine, propatheline, oxybutynin, S-oxybutynin, tizanidine, and mixtures thereof.
- the active compound is an agent for treating urinary incontinence.
- Suitable agents for treating urinary incontinence for use in the buccal sprays of the invention include, but are not limited to, darifenacin, vamicamide, detrol, ditropan, imipramine, and mixtures thereof.
- the active compound is an anti-diarrheal agent. Suitable anti-diarrheal agents for use in the buccal sprays of the invention include, but are not limited to, ondansetron, palnosetron, tropisetron, attapulgite, atropine, bismuth, diphenoxylate, loperamide, and mixtures thereof.
- the active compound is an agent for treating nausea and/or vomiting.
- Suitable agents for treating nausea and/or vomiting for use in the buccal sprays of the invention include, but are not limited to, alosetron, dolasetron, granisetron, meclizine, metoclopramide, ondansetron, palnosetron, prochloperazine, promethazine, trimethobenzamiode, tropisetron, and mixtures thereof.
- the active compound is a smooth muscle contractile agent.
- a suitable smooth muscle contractile agents for use in the buccal sprays of the invention includes, but is not limited to hyoscine.
- the active compound is an anti-secretory agent.
- Suitable anti-secretory agents for use in the buccal sprays of the invention include, but are not limited to, esomeprazole, lansoprazole, omeprazole, pantoprazole, rabeprazole, tenetoprazole, ecabet, misoprostol, teprenone, and mixtures thereof.
- the active compound is an enzyme.
- Suitable enzymes for use in the buccal sprays of the invention include, but are not limited to, alpha-galactosidase, alpha-L-iduronidase, imiglucerase/alglucerase, amylase, lipase, protease, pancreatin, olsalazine, and mixtures thereof.
- the active compound is an anti-diuretic.
- Suitable anti- diuretics for use in the buccal sprays of the invention include, but are not limited to, desmopressin, oxytocin, and mixtures thereof.
- the active compound is an anti-ulcerant.
- Suitable anti- ulcerants for use in the buccal sprays of the invention include, but are not limited to, cimetidine, ranitidine, famotidine, misoprostol, sucralfate, pantoprazole, lansoprazole, omeprazole, and mixtures thereof.
- the active compound is a bile acid replacement and/or gallstone solubilizmg drug.
- a suitable bile acid replacement and/or gallstone solubilizing drug for use in the buccal sprays of the invention includes, but is not limited to ursodiol.
- compositions of the present invention comprise an active compound or a pharmaceutically acceptable salt thereof.
- pharmaceutically acceptable salts refers to salts prepared from pharmaceutically acceptable non-toxic acids or bases including organic and inorganic acids or bases.
- salts maybe prepared from pharmaceutically acceptable non-toxic bases.
- Salts derived from all stable forms of inorganic bases include aluminum, ammonium, calcium, copper, iron, lithium, magnesium, manganese, potassium, sodium, zinc, etc. Particularly preferred are the ammonium, calcium, magnesium, potassium, and sodium salts.
- Salts derived from pharmaceutically acceptable organic non-toxic bases include salts of primary, secondary, and tertiary amines, substituted amines including naturally occurring substituted amines, cyclic amines and basic ion-exchange resins such as arginine, betaine, caffeine, choline, N,N dibenzylethylenediamine, diethylamine, 2-diethylaminoethanol, 2-dimethyl- aminoethanol, ethanolamine, ethylenediamine, N-ethylmorpholine, N-ethylpiperidine, glucamine, glucosamine, histidine, isopropylamine, lysine, methyl-glucosamine, morpholine, piperazine, piperidine, polyamine resins, procaine, purine, theobromine, triethylamine, trimethylamine, tripropylamine, etc.
- basic ion-exchange resins such as arginine, betaine, caffeine, choline, N
- salts maybe prepared from pharmaceutically acceptable non-toxic acids.
- acids include acetic, benzenesulfonic, benzoic, camphorsulfonic, citric, ethane-sulfonic, fumaric, gluconic, glutamic, hydrobromic, hydrochloric, isethionic, lactic, maleic, mandelic, methanesulfonic, mucic, nitric, pamoic, pantothenic, phosphoric, succinic, sulfuric, tartaric, p- toluenesulfonic, etc.
- Particularly preferred are citric, hydrobromic, maleic, phosphoric, sulfuric, and tartaric acids.
- Biolog ;ically active . peptides including peptide hormones
- Cyclosporine bite capsule Amounts preferred amount most preferred amount cyclosporine 1-35 5-25 10-20 olive oil 25-60 35-55 30-45 polyoxyethylated oleic glycerides 25-60 35-55 30-45 flavors 0.1-5 1-4 2-3 D. Cyclosporine bite capsule
- Amounts preferred amount most preferred sermorelin (as the acetate) .01-5 .1-3 .2-1.0 mannitol 1-25 5-20 10-15 monobasic sodium phosphate, 0.1-5 1-3 1 .5-2.5 dibasic sodium phosphate water 0.01-5 .05-3 0.1-0.5 ethanol 5-30 7.5-25 9.5-15 polyethylene glycol 20-60 30-45 35-40 propylene glycol 5-25 10-20 12-17 flavors 0.1-5 1-4 2-3
- Amounts preferred amount most preferred amount sumatriptan succinate 0.5-30 1-20 10-15 ethanol 5-60 7.5-50 10-20 propylene glycol 5-30 7.5-20 10-15 polyethylene glycol 0-60 30-45 35-40 water 5-30 7.5-20 10-15 flavors 0.1-5 1-4 2-3
- Amounts prefened amount most prefened amount ciprofloxacin hydrochloride 25-65 35-55 40-50 glycerin 5-20 7.5-15 10-12.5 polyethylene glycol 120-75 30-65 40-60 flavors 1-10 2-8 3-6
- Amoxuits prefened amount most prefened amount dimenhydrinate 0.5-30 2-25 3-15 glycerin 5-20 7.5-15 10-1 2.5 polyethylene glycol 45-95 50-90 55-85 flavors 1-10 2-8 3-6
- L-aspartic acid 0.1-20 1-15 5-10 polyethylene glycol 20-97 30-95 50-85 flavors 0.1-10 1-7.5 2-5
- pH is adjusted with sodium hydroxide and/or hydrochloric acid
- Promethazine antioxidant sleep inducer. and CNS active amine
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Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
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NZ539285A NZ539285A (en) | 2002-08-29 | 2003-08-27 | Buccal, polar and non-polar spray or capsule containing drugs for treating disorders of the gastrointestinal tract or urinary tract |
AU2003272242A AU2003272242A1 (en) | 2002-08-29 | 2003-08-27 | Buccal, polar and non-polar spray or capsule containing drugs for treating disorders of the gastrointestinal tract or urinary tract |
JP2004531570A JP2006506342A (en) | 2002-08-29 | 2003-08-27 | Buccal, polar and nonpolar sprays or capsules containing drugs to treat gastrointestinal or urinary tract disorders |
CA002497112A CA2497112A1 (en) | 2002-08-29 | 2003-08-27 | Buccal, polar and non-polar spray or capsule containing drugs for treating disorders of the gastrointestinal tract or urinary tract |
EP03754415A EP1534242A2 (en) | 2002-08-29 | 2003-08-27 | Buccal, polar or non-polar spray or capsule containing drugs for treating disorders of the gastrointestinal tract or urinary tract |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US10/230,085 | 2002-08-29 | ||
US10/230,085 US20030095926A1 (en) | 1997-10-01 | 2002-08-29 | Buccal, polar and non-polar spray or capsule containing drugs for treating disorders of the gastrointestinal tract or urinary tract |
Publications (2)
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WO2004019910A2 true WO2004019910A2 (en) | 2004-03-11 |
WO2004019910A3 WO2004019910A3 (en) | 2004-07-29 |
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PCT/US2003/026854 WO2004019910A2 (en) | 2002-08-29 | 2003-08-27 | Buccal, polar and non-polar spray or capsule containing drugs for treating disorders of the gastrointestinal tract or urinary tract |
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US (2) | US20030095926A1 (en) |
EP (1) | EP1534242A2 (en) |
JP (1) | JP2006506342A (en) |
AU (1) | AU2003272242A1 (en) |
CA (1) | CA2497112A1 (en) |
NZ (1) | NZ539285A (en) |
WO (1) | WO2004019910A2 (en) |
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Also Published As
Publication number | Publication date |
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AU2003272242A1 (en) | 2004-03-19 |
CA2497112A1 (en) | 2004-03-11 |
WO2004019910A3 (en) | 2004-07-29 |
US20050025716A1 (en) | 2005-02-03 |
EP1534242A2 (en) | 2005-06-01 |
NZ539285A (en) | 2007-10-26 |
JP2006506342A (en) | 2006-02-23 |
US20030095926A1 (en) | 2003-05-22 |
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